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Water → HCID 53692132, Verbindung

HRID 1078619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1078619
C(O)(=O)C(O)=O.C([O:11][C:12](=[O:26])[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:15]1=[O:25])(C)(C)C.[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:50](O)=[O:51])[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:27]([O:34][C:35]([NH:37][C@H:38]([C:50]([N:17]1[CH2:18][CH2:19][N:14]([CH2:13][C:12]([OH:11])=[O:26])[C:15](=[O:25])[C@@H:16]1[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:51])[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][CH:45]=1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10784543N-benzyloxycarbonyl-4-methoxycarbonyl-L-phenylalanineHCID 70048775HCID 70048775, Verbindung

Produkt 1

HCID 53692132HCID 53692132, VerbindungAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 7.6 ml of methylene chloride were dissolved 0.76 g of (S)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid t butyl ester oxalic acid salt and 0.47 g of N-benzyloxycarbonyl-4-methoxycarbonyl-L-phenylalanine. To the solution was added gradually, while cooling with water, 0.44 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, over 5 minutes. The mixture was stirred for one hour at room temperature, then methylene chloride was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed with a 5% aqueous solution of potassium hydrogensulfate and a saturated aqueous solution of hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by means of a silica gel chromatography (hexane/ethyl acetate=l/2) to give 0.46 g (51.1%) of the title compound as a colorless oily product.

Aufarbeitung

  1. additionTo the solution was added gradually
  2. distillationmethylene chloride was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed with a 5% aqueous solution of potassium hydrogensulfate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified by means of a silica gel chromatography (hexane/ethyl acetate=l/2)

Quellen und Nachweise

ORD-Eintrag
ord-ba1ca03f12df44af8180467148738fa9
Quelldatensatz
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05550131

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